Synthesis and crystal structures of N-Aryl-N-methylaminocyclohexanols

Alexander J. Cresswell, Stephen G. Davies, David S. Hewings, Wataru Kurosawa, James A. Lee, Melloney J. Morris, Paul M. Roberts, Amber L. Thompson, James E. Thomson

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

N-Aryl-N-methylaminocyclohexanols 10-12 were synthesised and their crystal structures were studied by X-ray diffraction. Compound 10 crystallizes in the monoclinic space group Cc with cell parameters of a = 13.7366(2) Å, b = 13.7234(2) Å, c = 26.9057(5) Å, β = 93.0900(5), V = 5064.70(14) Å3 and Z = 16. Compound 11 crystallizes in the trigonal space group P 3 ̄ with cell parameters of a = b = 25.4429(4) Å, c = 9.6417(2) Å, V = 5405.27(16) Å3 and Z = 18. Compound 12 crystallizes in the monoclinic space group P21/n with cell parameters of a = 9.9511(2) Å, b = 11.5777(2) Å, c = 20.5968(4) Å, β = 95.5037(9), V = 2362.04(8) Å3 and Z = 8. All three structures were characterised by arrays of hydrogen bonding interactions and these crystallographic studies revealed conformations of 10-12 which gave valuable information into the mechanism of the reaction during their formation. Graphical Abstract: Crystals of (RS,RS,RS)-3-[N-methyl-N-(4'-methoxyphenyl) amino]cyclohexane-1,2-diol, (RS,RS,RS)-3-(N-methyl-N-phenylamino)cyclohexane-1, 2-diol and (RS,RS,RS)-2-fluoro-6-(N-methyl-N-phenylamino)cyclohexan-1-ol were synthesised and their structures were studied by X-ray diffraction.[Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)646-654
Number of pages9
JournalJournal of Chemical Crystallography
Volume43
Issue number12
DOIs
Publication statusPublished - Dec 2013

Keywords

  • Amino alcohol
  • Dihydroxylation
  • Hydrogen bonding
  • Hydroxyfluorination
  • Olefinic oxidation

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics

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